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In the title compound, C11H13NOS, the thio­phene ring is planar while the central six-membered ring has a half-chair conformation and the second ring of the quinolizine moiety is in a chair conformation. The angles at the N atom sum to 331.22°, indicating pyramidalization of this atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805003454/kp6040sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805003454/kp6040Isup2.hkl
Contains datablock I

CCDC reference: 269802

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.037
  • wR factor = 0.114
  • Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 3.16 Sigma
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: KM-4 Software (Kuma, 1992); cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

5,6,7,8-tetrahydro-4aH-thieno[3,2-b]quinolizin-4(10H)-one top
Crystal data top
C11H13NOSF(000) = 440
Mr = 207.28Dx = 1.357 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2238 reflections
a = 6.808 (2) Åθ = 2.3–34.1°
b = 18.770 (9) ŵ = 0.28 mm1
c = 8.256 (3) ÅT = 298 K
β = 105.84 (3)°Prism, colorless
V = 1014.9 (7) Å30.60 × 0.50 × 0.30 mm
Z = 4
Data collection top
Kuma KM-4 CCD
diffractometer
1765 reflections with F2 > 2σ(F2)
Radiation source: fine-focus sealed tubeRint = 0.034
Graphite monochromatorθmax = 27.1°, θmin = 2.2°
ω scansh = 88
8775 measured reflectionsk = 240
2238 independent reflectionsl = 105
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0629P)2 + 0.1855P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
2238 reflectionsΔρmax = 0.40 e Å3
128 parametersΔρmin = 0.25 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0060 (19)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C20.2977 (3)0.03415 (9)0.1691 (2)0.0562 (4)
H20.30720.01490.18580.067*
C30.1215 (3)0.07026 (8)0.1324 (2)0.0462 (4)
H30.00550.04940.12110.055*
C40.0034 (2)0.19918 (8)0.05778 (18)0.0373 (3)
C50.0812 (2)0.32880 (8)0.0739 (2)0.0441 (4)
H5A0.21220.32180.00800.053*
H5B0.09940.32120.18510.053*
C60.0091 (3)0.40474 (9)0.0610 (2)0.0512 (4)
H6A0.00720.41460.05390.061*
H6B0.10270.43790.09090.061*
C70.2027 (3)0.41451 (8)0.1781 (2)0.0537 (4)
H7A0.19710.41040.29390.064*
H7B0.25250.46180.16280.064*
C80.3481 (3)0.35896 (8)0.1435 (2)0.0475 (4)
H8A0.36270.36590.03090.057*
H8B0.48150.36500.22270.057*
C90.4245 (2)0.23644 (8)0.1264 (2)0.0398 (3)
H9A0.55530.24360.20840.048*
H9B0.44190.24480.01510.048*
C100.1524 (2)0.14472 (7)0.11284 (17)0.0360 (3)
C110.0714 (2)0.27471 (7)0.04268 (16)0.0339 (3)
H110.08130.28130.07260.041*
C130.3526 (2)0.16222 (8)0.13807 (17)0.0370 (3)
S10.50491 (7)0.08858 (2)0.18172 (7)0.05591 (18)
O140.18523 (17)0.18518 (7)0.0166 (2)0.0637 (4)
N120.27451 (17)0.28635 (6)0.15825 (14)0.0346 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0660 (11)0.0333 (8)0.0708 (12)0.0014 (7)0.0210 (9)0.0036 (7)
C30.0536 (9)0.0372 (7)0.0512 (9)0.0082 (6)0.0201 (7)0.0042 (6)
C40.0343 (7)0.0402 (7)0.0393 (7)0.0027 (6)0.0134 (6)0.0047 (6)
C50.0414 (8)0.0435 (8)0.0486 (8)0.0084 (6)0.0144 (6)0.0038 (6)
C60.0604 (10)0.0385 (8)0.0556 (10)0.0109 (7)0.0172 (8)0.0067 (7)
C70.0681 (11)0.0340 (8)0.0561 (10)0.0007 (7)0.0118 (8)0.0035 (7)
C80.0469 (8)0.0355 (8)0.0579 (10)0.0073 (6)0.0105 (7)0.0010 (7)
C90.0317 (6)0.0381 (7)0.0507 (8)0.0014 (6)0.0127 (6)0.0000 (6)
C100.0405 (7)0.0333 (7)0.0361 (7)0.0030 (6)0.0134 (6)0.0042 (5)
C110.0342 (7)0.0375 (7)0.0305 (6)0.0009 (5)0.0097 (5)0.0007 (5)
C130.0366 (7)0.0350 (7)0.0393 (7)0.0026 (5)0.0105 (6)0.0010 (5)
S10.0456 (3)0.0408 (3)0.0784 (4)0.00987 (16)0.0120 (2)0.00354 (19)
O140.0330 (6)0.0544 (7)0.1013 (11)0.0064 (5)0.0145 (6)0.0049 (7)
N120.0341 (6)0.0310 (6)0.0375 (6)0.0019 (4)0.0077 (5)0.0011 (4)
Geometric parameters (Å, º) top
C2—C31.339 (2)C7—C81.518 (2)
C2—S11.7214 (19)C7—H7A0.9700
C2—H20.9300C7—H7B0.9700
C3—C101.429 (2)C8—N121.4687 (19)
C3—H30.9300C8—H8A0.9700
C4—O141.2196 (18)C8—H8B0.9700
C4—C101.454 (2)C9—N121.4617 (18)
C4—C111.523 (2)C9—C131.489 (2)
C5—C61.521 (2)C9—H9A0.9700
C5—C111.524 (2)C9—H9B0.9700
C5—H5A0.9700C10—C131.362 (2)
C5—H5B0.9700C11—N121.4660 (18)
C6—C71.512 (3)C11—H110.9800
C6—H6A0.9700C13—S11.7062 (16)
C6—H6B0.9700
C3—C2—S1112.47 (13)N12—C8—H8A109.3
C3—C2—H2123.8C7—C8—H8A109.3
S1—C2—H2123.8N12—C8—H8B109.3
C2—C3—C10111.71 (15)C7—C8—H8B109.3
C2—C3—H3124.1H8A—C8—H8B108.0
C10—C3—H3124.1N12—C9—C13109.25 (11)
O14—C4—C10122.28 (14)N12—C9—H9A109.8
O14—C4—C11120.97 (14)C13—C9—H9A109.8
C10—C4—C11116.63 (12)N12—C9—H9B109.8
C6—C5—C11111.40 (13)C13—C9—H9B109.8
C6—C5—H5A109.3H9A—C9—H9B108.3
C11—C5—H5A109.3C13—C10—C3113.01 (13)
C6—C5—H5B109.3C13—C10—C4119.51 (13)
C11—C5—H5B109.3C3—C10—C4127.28 (13)
H5A—C5—H5B108.0N12—C11—C4111.26 (11)
C7—C6—C5109.77 (13)N12—C11—C5110.86 (12)
C7—C6—H6A109.7C4—C11—C5110.33 (11)
C5—C6—H6A109.7N12—C11—H11108.1
C7—C6—H6B109.7C4—C11—H11108.1
C5—C6—H6B109.7C5—C11—H11108.1
H6A—C6—H6B108.2C10—C13—C9123.30 (13)
C6—C7—C8110.69 (14)C10—C13—S1111.23 (11)
C6—C7—H7A109.5C9—C13—S1125.47 (11)
C8—C7—H7A109.5C13—S1—C291.57 (8)
C6—C7—H7B109.5C9—N12—C11111.62 (11)
C8—C7—H7B109.5C9—N12—C8107.99 (12)
H7A—C7—H7B108.1C11—N12—C8111.51 (12)
N12—C8—C7111.53 (14)
S1—C2—C3—C100.24 (19)C4—C10—C13—C95.4 (2)
C11—C5—C6—C754.44 (19)C3—C10—C13—S11.17 (16)
C5—C6—C7—C854.5 (2)C4—C10—C13—S1173.98 (10)
C6—C7—C8—N1256.8 (2)N12—C9—C13—C1024.4 (2)
C2—C3—C10—C130.9 (2)N12—C9—C13—S1156.27 (11)
C2—C3—C10—C4173.78 (15)C10—C13—S1—C20.88 (12)
O14—C4—C10—C13172.27 (15)C9—C13—S1—C2179.76 (14)
C11—C4—C10—C133.84 (19)C3—C2—S1—C130.36 (15)
O14—C4—C10—C32.1 (2)C13—C9—N12—C1156.30 (16)
C11—C4—C10—C3178.23 (13)C13—C9—N12—C8179.20 (12)
O14—C4—C11—N12156.36 (14)C4—C11—N12—C958.75 (14)
C10—C4—C11—N1227.47 (16)C5—C11—N12—C9178.07 (11)
O14—C4—C11—C532.89 (19)C4—C11—N12—C8179.63 (11)
C10—C4—C11—C5150.94 (13)C5—C11—N12—C857.20 (16)
C6—C5—C11—N1255.82 (17)C7—C8—N12—C9178.92 (14)
C6—C5—C11—C4179.53 (13)C7—C8—N12—C1158.11 (18)
C3—C10—C13—C9179.45 (14)
 

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